Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for producing 1,3-dimethyladamantane

a technology of dimethyladamantane and 1,3-dimethyladamantane, which is applied in the direction of organic chemistry, chemical apparatus and processes, hydrocarbon preparation catalysts, etc., can solve the problems of low yield of 38.7%, high cost of pt and re in the catalyst, and no selective production method of 1,3-dimethyladamantane at a high yield by using hf.bf/sub>catalys

Active Publication Date: 2015-07-21
MITSUBISHI GAS CHEM CO INC
View PDF27 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0024]According to a method of the present invention, no solvent is used. Therefore, a step of removing a solvent and a denatured substance thereof is not necessary. In addition, no costly catalyst is required, and a catalyst used can be recovered. Thus, 1,3-dimethyladamantane can be produced at a high yield and advantageously in terms of cost while environmental load is reduced.

Problems solved by technology

However, the method of obtaining 1,3-dimethyladamantane from PHA has problems that the yield is as low as 38.7% and that Pt and Re in the catalyst are costly.
However, no method of selectively producing 1,3-dimethyladamantane at a high yield by use of HF.BF3 catalysts is known so far.
However, in order to obtain 1,3-dimethyladamantane at a high yield, it is indispensable to use 1,2-dichloroethane, which is costly, as a catalyst component.
In addition, aluminum chloride is not reusable and thus a large amount of waste derived from aluminum chloride is generated.
For these reasons, the method of using aluminum chloride is not industrially advantageous (Patent Document 5).

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Method for producing 1,3-dimethyladamantane
  • Method for producing 1,3-dimethyladamantane
  • Method for producing 1,3-dimethyladamantane

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0044]PHA was subjected to an isomerization reaction by use of a Hastelloy autoclave having a capacity of 0.5 L and including an electromagnetic stirring device, a heating device, a gas and liquid supply opening and a reaction product discharge opening. 50 g (2.5 mol) of HF produced by Morita Chemical Industries Co., Ltd. and 100 g (0.6 mol) of PHA were put to a reactor, and 16 g (0.24 mol) of BF3 produced by Stella Chemifa Corporation was supplied. Then, these substances were heated to a temperature of 100° C. by the heating device with no solvent, and stirred for 4 hours while the temperature was kept at 100° C. The reaction product solution was sampled. The yield of 1,3-dimethyladamantane was 77% with respect to PHA as the material. The yield of 1-ethyladamantane as an intermediate was 15% with respect to PHA as the material, while no high boiling point compound was observed. Then, as a result of being left still, the reaction product solution was divided into two layers, namely,...

example 2

[0045]A reaction was carried out under substantially the same conditions as those in Example 1 except that HF and BF3 recovered in Example 1 were used. The yield of 1,3-dimethyladamantane was 75%, and deactivation of the catalysts was not observed. Like in Example 1, no high boiling point compound was observed.

example 3

[0046]PHA was subjected to an isomerization reaction by use of a Hastelloy autoclave having a capacity of 0.5 L and including an electromagnetic stirring device, a heating device, a gas and liquid supply opening and a reaction product discharge opening. 50 g (2.5 mol) of HF produced by Morita Chemical Industries Co., Ltd. and 100 g (0.6 mol) of PHA were put to a reactor, and 16 g (0.24 mol) of BF3 produced by Stella Chemifa Corpration was supplied. Then, these substances were heated to a temperature of 80° C. by the heating device with no solvent, and stirred for 4 hours while the temperature was kept at 80° C. The reaction product solution was sampled. The yield of 1,3-dimethyladamantane was 51% with respect to PHA as the material. The yield of 1-ethyladamantane as an intermediate was 42% with respect to PHA as the material, while no high boiling point compound was observed. Then, as a result of being left still, the reaction product solution was divided into two layers, namely, an...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
temperatureaaaaaaaaaa
temperatureaaaaaaaaaa
temperatureaaaaaaaaaa
Login to View More

Abstract

According to the present invention, a method can be provided for producing 1,3-dimethyladamantane represented by formula (2) by performing a skeletal isomerization reaction using, as catalysts, 0.5 to 1 .5 parts by weight of HF and 0.05 to 0.5 parts by weight of BF3 with respect to 1 part by weight of perhydroacenaphthene represented by formula (1) under a reaction temperature of 60 to 110° C.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This Application is a U.S. National Stage Application filed under 35 U.S.C. §371 of International Application PCT / JP2011 / 075694, filed Nov. 8, 2011, designating the United States, which claims priority from Japanese Patent Application 2010-254189, filed Nov. 12, 2010, the complete disclosures of which are hereby incorporated herein by reference in their entirety for all purposes.TECHNICAL FIELD[0002]The present invention relates to a method for producing 1,3-dimethyladamantane represented by the following formula (2) industrially advantageously from perhydroacenaphthene represented by the following formula (1) by use of HF.BF3 catalysts.[0003]BACKGROUND ART[0004]1,3-dimethyladamantane is expected to be useful as a material of various types of fine chemicals including pharmaceutical drugs, and a dicarboxylic acid and a diol thereof are expected to be useful as a highly functional polymer material.[0005]Conventionally, Patent Document 1 des...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(United States)
IPC IPC(8): C07C13/28C07C5/31C07C5/29
CPCC07C5/31C07C5/29C07C13/615C07C2103/20C07C2103/74C07C2527/1206C07C2527/1213C07C2603/20C07C2603/74C07C5/22C07B61/00
Inventor MATSUURA, YUTAKAKITAMURA, MITSUHARU
Owner MITSUBISHI GAS CHEM CO INC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com